Expansion of indolizine chemical space -Dirgha.pptx

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Expansion of indolizine chemical space via construction of poly-functionalized pyridines: A oral presentation delivered to American Chemical Society Conference.

Health & Medicine

Dirgha Raj Joshi
PhD Candidate
Medicinal Chemistry lab,
College of Pharmacy, Yonsei University
Email: djmeropaila121@yonsei.ac.kr
Expansion of indolizine chemical space
via construction of poly-functionalized pyridines
Supervisor: Prof. Ikyon Kim, Ph.D.
Indolizine
Bonding Through Chemistry, ACS Spring 2022, March 20 – 24, San Diego, USA

Research Topics
M. Scholtz, Chem. Ber., 1912, 45, 734
First discovery of indolizine in 1890
A. Angeli, Gazz. Chim. Iial. 1890, 26, 1793
EJMC, 2011, 46, 5237-5257
Joshi & Kim; J. Org. Chem. 2020, 85, 10994–11005
Discovery and Construction of Indolizine Some Biologically Active Indolizines
First synthesis of indolizine by Scholtz in 1912

Domino [4 + 2] Annulation Access to Quinone-Indolizine Hybrids: Anticancer N-Fused Polycycles
Joshi & Kim; J. Org. Chem. 2020, 85, 10994–11005.
Joshi & Kim; J. Org. Chem. 2021, 86, 15, 10235–10248.
Michael-Aldol Double Elimination Cascade to Make Pyridines: Use of Chromone for the Synthesis of Indolizines
Inspiration from our successful annulations

Tetrahedron 2018, 74, 6088−6094
Joshi & Kim; Adv. Syn. Cat., 2021, 363, 23, 5330-5335
[5+1] Annulative Access to Pyridines

entry base (equiv) solvent Temper. (°C) time (h) yield (%)
1 Cs2CO3 (2) CH3CN 120 24 39
2 K2CO3 (2) CH3CN 120 24 5
3 Na2CO3 (2) CH3CN 120 24 NR
4 Et3N (2) CH3CN 120 24 NR
5 DBU (2) CH3CN 120 24 15
6 Cs2CO3 (1.5) CH3CN 130 12 68
7 Cs2CO3 (1.5) DMSO 130 12 65
8 Cs2CO3 (1.5) 2-MeTHF 130 6 85
9 Cs2CO3 (1.5) THF 130 24 NR
10 Cs2CO3 (1.5) 2-MeTHF 130 12 68 (gm scale)
Reaction Optimization

7b (78%)
R= OMe, 7c (71%)
R= Me, 7d (79%)
7e (80%) 7f (83%) 7g (81%) 7h (83%) 7i (73%)
Reaction Scope
7j (78%) 7k (86%) 7l (73%) 7m (67%) 7n (63%) 7o (33%) 7p (78%) 7q (85%)
7r (81%) 7s (73%) 7t (75%) 7u (71%) 7v (78%)
7s
R1=OMe, R2=Cl, 7w (77%)
R1=Cl, R2=Br, 7x (72%)

Use of Other Methyl Ketones
Oxidation of Dihydroindolizinesa
a dry THF and added NatBuO (1.2 to 3 equiv.) at rt

Acknowledgement
• Prof. Ikyon Kim: Ph.D. Supervisor
• Prof. Hak Sung Kim: Master’s Supervisor
• Yonsei University: for providing Global Leader Scholarship & ARF
• Lab members
Bonding Through Chemistry, ACS Spring 2022, March 20 – 24, San Diego, USA

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Photocatalysis has now become an emerging scientific discipline due to its interdisciplinary nature. The wide range of research groups is now working on different aspects of photocatalysis worldwide. It is one of the technology the world looking forward to address environmental as well as energy related issues. Hence we can call it as a technology for the future or a dream technology! We need to overcome too many hurdles to implement this technology in real life. Like any other discipline there is a lot of misunderstanding/ misconceptions in photocatalysis. Most frequently cited article in the field of photocatalysis is by Fujishima and Honda published in 1972 in nature and it has been cited by the photocatalytic community as an origin of photocatalysis. This aspect is not true at all. This article cannot be the origin of photocatalysis. This article only promoted photocatalytic studies. The author itself, actually, started a research career in the “boom” of photocatalytic studies initiated by this article. This small presentation aims to deliver some misconceptions like above in photocatalysis. The entire presentation is based on different personal commentaries written by Jean Mary Hermann and Bunsho Ohtani. Some recent articles relevant to the topic are collected by the speaker itself and put it in one platform.

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Expansion of indolizine chemical space -Dirgha.pptx

1. Dirgha Raj Joshi PhD Candidate Medicinal Chemistry lab, College of Pharmacy, Yonsei University Email: djmeropaila121@yonsei.ac.kr Expansion of indolizine chemical space via construction of poly-functionalized pyridines Supervisor: Prof. Ikyon Kim, Ph.D. Indolizine Bonding Through Chemistry, ACS Spring 2022, March 20 – 24, San Diego, USA

2. Research Topics M. Scholtz, Chem. Ber., 1912, 45, 734 First discovery of indolizine in 1890 A. Angeli, Gazz. Chim. Iial. 1890, 26, 1793 EJMC, 2011, 46, 5237-5257 Joshi & Kim; J. Org. Chem. 2020, 85, 10994–11005 Discovery and Construction of Indolizine Some Biologically Active Indolizines First synthesis of indolizine by Scholtz in 1912

3. Domino [4 + 2] Annulation Access to Quinone-Indolizine Hybrids: Anticancer N-Fused Polycycles Joshi & Kim; J. Org. Chem. 2020, 85, 10994–11005. Joshi & Kim; J. Org. Chem. 2021, 86, 15, 10235–10248. Michael-Aldol Double Elimination Cascade to Make Pyridines: Use of Chromone for the Synthesis of Indolizines Inspiration from our successful annulations

4. Tetrahedron 2018, 74, 6088−6094 Joshi & Kim; Adv. Syn. Cat., 2021, 363, 23, 5330-5335 [5+1] Annulative Access to Pyridines

5. entry base (equiv) solvent Temper. (°C) time (h) yield (%) 1 Cs2CO3 (2) CH3CN 120 24 39 2 K2CO3 (2) CH3CN 120 24 5 3 Na2CO3 (2) CH3CN 120 24 NR 4 Et3N (2) CH3CN 120 24 NR 5 DBU (2) CH3CN 120 24 15 6 Cs2CO3 (1.5) CH3CN 130 12 68 7 Cs2CO3 (1.5) DMSO 130 12 65 8 Cs2CO3 (1.5) 2-MeTHF 130 6 85 9 Cs2CO3 (1.5) THF 130 24 NR 10 Cs2CO3 (1.5) 2-MeTHF 130 12 68 (gm scale) Reaction Optimization

6. 7b (78%) R= OMe, 7c (71%) R= Me, 7d (79%) 7e (80%) 7f (83%) 7g (81%) 7h (83%) 7i (73%) Reaction Scope 7j (78%) 7k (86%) 7l (73%) 7m (67%) 7n (63%) 7o (33%) 7p (78%) 7q (85%) 7r (81%) 7s (73%) 7t (75%) 7u (71%) 7v (78%) 7s R1=OMe, R2=Cl, 7w (77%) R1=Cl, R2=Br, 7x (72%)

7. Conversion of 7f’ to 7f Derivatization

8. Control Experiments Proposed Mechanism

9. Use of Other Methyl Ketones Oxidation of Dihydroindolizinesa a dry THF and added NatBuO (1.2 to 3 equiv.) at rt

10. Conclusion

11.

12. Acknowledgement • Prof. Ikyon Kim: Ph.D. Supervisor • Prof. Hak Sung Kim: Master’s Supervisor • Yonsei University: for providing Global Leader Scholarship & ARF • Lab members Bonding Through Chemistry, ACS Spring 2022, March 20 – 24, San Diego, USA

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